In 1996, there were a lot more passenger trains in this country. There were daily trips between Victoria and Courtenay and between North Vancouver and Prince George via 100 Mile House to name a few. But the evisceration of VIA Rail was just getting going with the Chrétien government’s third budget. It was hard to guess which train lines would vanish when, so my friend Oscar and I thought I had better take the train trip that had fascinated me the most: the Winnipeg-Churchill run through the entire breadth of Canada’s boreal forest and across the tree line. It was a great trip in which I watched Oscar swim in the Arctic Ocean and looked at amazing comic book-style ivory dioramas of Inuit legends; it’s one that I hope people can still make when another two thirds of VIA’s funding is cut by Harper in the next fiscal year.

But the thing I remember best about it was dropping in on my friend K at the 1996 Progressive Conservative Party convention in Winnipeg on the way. He and my other Tory friends had been crushed by the party’s annihilation in 1993 personally, financially, ideologically, you name it. But they were young and not prepared to give up. When I arrived, it was late on the Friday night and people were in high spirits. I began asking where K was and was directed to a ballroom on the top floor of the convention hotel, where he and New Brunswick Opposition leader Bernard Valcourt were in finalists in the convention’s “bungee running” competition.

As though re-enacting the entire post-Mulroney experience of the party in a single cathartic episode, K, former Special Assistant to the Speaker and Valcourt, disgraced former cabinet minister were tied to the wall on opposite sides of the room with long bungee cords and were competing to stretch their cords far enough, fast enough to reach the bottle of single malt scotch on top of a makeshift plinth in the centre of the room – but not so fast that the cord snapped them back to the wall. Auguring things to come, Valcourt got the bottle and shared a small amount of it with K before putting me in a celebratory introductory headlock and staggering downstairs.

Then I asked K how the convention had gone and he was ebullient. Having made Jean Charest party leader, he felt confident the Tories would (as they did) regain official party status in 1997 and believed that, with hard work, they could form the Official Opposition. (They failed to do that but did get a fifth of the popular vote, the second largest share in the election and more than half of the victorious Liberals’.) The reason he was confident, he explained, was that the convention comprised only two main groups of delegates: people who shared his clear-eyed vision of how the party could claw its way, incrementally, back to relevance and less clear-headed delegates who were “on side for the big win.”

The reason K felt confident in the party’s recovery was that, while forming a core of dedicated donors and volunteers, those On Side for the Big Win were not crafting election strategy. The term soon joined my vocabulary as a crucial descriptor for a certain kind of activist as I entered my second term as BC Green Party leader.

But by 1999, the term had taken on a less rosy complexion in our shared lexicon. K and his allies were fighting off a takeover attempt by David Orchard (something I’d advised Orchard to do over dinner in 1997 as a media stunt). Orchard’s supporters were utterly humourless and totally convinced that, upon their guru’s election as party leader, the Tories would surge into first place and form a majority government. I, meanwhile, was fighting off a leadership challenge by Adriane Carr who confidently proclaimed to anyone who would listen that once people saw her in the televised debate, she would become premier of BC.

It was tough for K and me, in our respective parties, to challenge prescriptions of sudden, easy, total victory because so damned many people were On Side for the Big Win. Why, such people wanted to know, was I trying to build electoral alliances with labour and New Democrats? Why was I diverting energy from suburban ridings into a handful of city centre and hippie-filled wet belt rural seats? These kinds of compromises and sacrifices seemed insane to people who imagined total victory to be just around the corner.

But I want to suggest that this desperate conviction of total, imminent victory in the face of overwhelming evidence, like having less than 1000 members in your party and a budget of less than $70,000 per year, is not really optimism at all. It is actually the most pernicious manifestation of despair one can find.

Magical thinking – see my article on this elsewhere – emerges most often when people lose the ability to imagine an actual, real, plausible path to what they want and they retreat into a kind of conscious, dissociative fantasy life in which they replace real world improvement with an imaginary future in which they take refuge from the bleak realities that surround them.

Nobody has ever been more On Side for the Big Win than the Native Americans who joined the Ghost Dance movement of the prophet Wovoka who promised victory in battle through invincibility to bullets and European disease and divine assistance in a rectifying eschaton that would cleanse the Americas of colonists. The false, desperate confidence of those who rode into battle to die during the closing of the frontier in the 1880s was not actual hope – it was total and abject despair.

Today, many of us on the Civic Left are caught between two kinds of despair: a cynical and hopeless politics of brokerage and collaboration with corporate real estate elites on one hand and the politics of the Big Win on the other. To follow either path is to succumb to despair.

I – and a growing coalition of people I meet every day – can see a narrow, hard, steep path for this city’s left to recover, to stand against the escalating efforts to cleanse the city of all but the wealthiest among us. But we must keep our wits about us. We are not on an inexorable march to victory any more than we have been permanently defeated – there is hope but that hope is fragile, evidence-based and meriting careful analysis and clever strategy. But we must guard against that hope turning to desperation and ourselves, our friends and allies coming On Side for the Big Win.